Triarylamine-based compound, method of preparing the same, and organic light emitting device using the triarylamine-based compound

Abstract

A triarylamine-based compound of formula 1, a method of preparing the same, and an organic light emitting device including the triarylamine-based compound of formula 1: where Ar 1 through Ar 4 are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; R is a halogen atom, a cyano group, a substituted or unsubstituted C1-C30 alkyl group; n is an integer of 1 through 3; and m is an integer of 1 through 3. The triarylamine-based compound of formula 1 has excellent electrical properties and a great charge transporting capability. An organic light emitting device including an organic layer formed of the triarylamine-based compound has high efficiency, low operating voltage, great luminance, and long lifetime.

1. An organic light emitting device, comprising:
 a first electrode; 
 a second electrode; and 
 an organic layer interposed between the first electrode and the second electrode, the organic layer comprising a triarylamine-based compound represented by one of formulae 2-4: 
 
       
         
           
           
               
               
           
         
         where Ar 1  through Ar 4  are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; and 
         each R is independently a C1-C30 alkyl group. 
       
     
     
       2. The organic light emitting device of  claim 1 , wherein the organic layer is at least one selected from the group consisting of a hole injection layer, a hole transport layer, and an emission layer. 
     
     
       3. The organic light emitting device of  claim 1 , wherein the organic layer comprises a layer having hole injecting and hole transporting capabilities. 
     
     
       4. A method of preparing a triarylamine-based compound of one of formulae 2-4: 
       
         
           
           
               
               
           
         
         where Ar 1  through Ar 4  are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; and 
         each R is independently a C1-C30 alkyl group, 
         the method comprising: 
         reacting compounds of formulae 8 through 10: 
       
       
         
           
           
               
               
           
         
         where Ar 1  through Ar 4  are independently a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group; and 
         each R is independently a C1-C30 alkyl group. 
       
     
     
       5. The method of  claim 4 , wherein the reaction is performed in the presence of tri(dibenzylideneacetone)dipalladium(0) at a reaction temperature of 50 to 150° C. 
     
     
       6. The method of  claim 4 , wherein the compound of formula 8 is prepared by reacting a compound of formula 11 with butyl lithium and then by reacting the resultant product with copper chloride: 
       
         
           
           
               
               
           
         
         where R is a C1-C30 alkyl group. 
       
     
     
       7. The method of  claim 6 , wherein the reaction temperature for the preparation of the compound of formula 8 is in the range of −78° C. to 0° C. 
     
     
       8. An organic light emitting device, comprising:
 a first electrode; 
 a second electrode; and 
 an organic layer interposed between the first electrode and the second electrode, the organic layer comprising a triarylamine-based compound prepared by the method of  claim 4 . 
 
     
     
       9. The organic light emitting device of  claim 8 , wherein the reacting of the compounds of formulae 8 through 10 is performed in the presence of tri(dibenzylideneacetone)dipalladium(0) at a reaction temperature of 50° C. to 150° C. 
     
     
       10. The organic light emitting device of  claim 8 , wherein the compound of formula 8 is prepared by reacting a compound of formula 11 with butyl lithium and then by reacting the resultant product with copper chloride: 
       
         
           
           
               
               
           
         
         where R is a C1-C30 alkyl group. 
       
     
     
       11. The organic light emitting device of  claim 10 , wherein the reaction temperature for the preparation of the compound of formula 8 is in the range of −78° C. to 0° C. 
     
     
       12. The organic light emitting device of  claim 1 , wherein the triarylamine-based compound is represented by formula 2: 
       
         
           
           
               
               
           
         
         where Ar 1  through Ar 4  are as described in  claim 14 , and R is a C1-C10 alkyl group. 
       
     
     
       13. The organic light emitting device of  claim 1 , wherein the triarylamine-based compound is represented by formula 3: 
       
         
           
           
               
               
           
         
         where each of Ar 1  through Ar 4  is as described in  claim 14 , and R is a C1-C10 alkyl group. 
       
     
     
       14. The organic light emitting device of  claim 1 , wherein the triarylamine-based compound is represented by formula 4: 
       
         
           
           
               
               
           
         
         where each of Ar 1  through Ar 4  is as described in  claim 14 , and R is a C1-C10 alkyl group. 
       
     
     
       15. The organic light emitting device of  claim 1 , wherein the triarylamine-based compound is selected from the group consisting of the compounds represented by formulae below: